Celebrate the season with festive live concerts every Friday with the Millennium Park Holiday Sing-Along starting on December 5, 12 and 19, 2025. Join a diverse group of choirs and ensembles as they light up the park with music. The holiday Sing-Along kicks off on Fridays from 6-7 pm, right … [Read more...] about Millennium Park Holiday Sing-Alongs
live music
Lakeview East Art Festival
The 20th annual Lakeview East Festival of the Arts showcases an exciting range of visual arts and live music on two stages in the Lakeview neighborhood on September 13-14, 2025. Explore a line-up of 150 juried artists from around the country displaying everything from paintings, … [Read more...] about Lakeview East Art Festival
Free Thirsty Ears Classical Music Fest
Enjoy the beautiful melodies, cultural traditions and welcoming community of Chicago's only classical music festival, the Thirsty Ears Festival on August 23-24, 2025. The 10th annual event supplies two days of classical music, food vendors, craft beer and kids' activities in the … [Read more...] about Free Thirsty Ears Classical Music Fest
Jeff Fest Arts and Music Festival
The Jefferson Park neighborhood on Chicago's Northwest side will come alive with music and creative arts during the 24th annual Jeff Fest, on August 1-2, 2025. The sprawling seven acres of Jefferson Memorial Park will host this beloved community event, which features tribute bands, … [Read more...] about Jeff Fest Arts and Music Festival
Passport Vibes: Afrobeat Street Festival
Dance to the joyful, contagious rhythms of Afrobeat music during the free Afrobeat Street Festival on July 13, 2025, in the Hyde Park neighborhood. Explore the culture of Afrobeat, a genre created in Nigeria by the legendary musician Fela Kuti, with DJs from around the world … [Read more...] about Passport Vibes: Afrobeat Street Festival
Andersonville Vintage Market
The Chicago shopping event of the summer returns; the fifth annual Andersonville Vintage Market will supply treasures from every era on select Sundays on July 20, August 17. September 21 and October 19, 2025. Discover one-of-a-kind antiques, jewelry, furniture, art, clothing and more at … [Read more...] about Andersonville Vintage Market
Ravenswood on Tap
Head to Malt Row, Ravenswood's bustling craft beer community to sip your way through the annual Ravenswood on Tap festival on July 19 - 20, 2025. The festival showcases the neighborhood's small craft breweries, including Koval, Dovetail, Half Acre and more. Enjoy fresh brews and cocktails as … [Read more...] about Ravenswood on Tap
Tacos Y Tamales Festival
Taste the delicious Mexican food traditions of authentic tacos and tamales at the inaugural Tacos Y Tamales Festival on July 18-20, 2025, in the Pilsen neighborhood. Experience a variety of Latin American cultural highlights at this free, three-day festival. Sample different tamales … [Read more...] about Tacos Y Tamales Festival
International Festival of Life
Enjoy the global rhythms of reggae, African and Latin music at the 32nd annual African/ Caribbean International Festival of Life, July 11-13, 2025. Dive into the music, food and art of different cultures during this beloved event in the South Loop. The headliners for this … [Read more...] about International Festival of Life
Wicker Park Fest
Music lovers never want to miss the eclectic music line-up of Wicker Park Fest, scheduled for July 25-27, 2025. This popular neighborhood fest draws visitors from across the country who love cutting-edge sounds and funky arts and crafts vendors. Trendy Wicker Park has been the headquarters … [Read more...] about Wicker Park Fest
Wells Street Art Festival
The historic Old Town neighborhood comes alive with the highly anticipated Wells Street Art Festival on June 14 and 15, 2025, in the heart of the landmark neighborhood Traditionally held on the second weekend in June, the fair features artists from all over North America, including painters, … [Read more...] about Wells Street Art Festival
Lincoln Park Greek Fest
Enjoy the flavors, sounds and sights of Greek culture at the popular Lincoln Park Greek Fest on June 6-8, 2025. The annual cultural festival features authentic Greek food, music, dancing and a craft fair on the grounds of St. George Greek Orthodox Church Traditional Greek dishes … [Read more...] about Lincoln Park Greek Fest
